Some high-end STR's (like in Joshua Tree) do use professional models, but for your market and property type, I’d suggest removing personal photos and focusing on the space itself, so guests can imagine themselves there, which is really what you want.You also have 81 photos, that’s too many.

The drawback is you need to build trust and relationships upfront.Both have their place, but private money tends to offer more flexibility, while hard money is more structured and accessible if you lack personal connections.

Nice to connect 😎Its in Joliet - Cathedral area I hope to meet you in person as well?

I had another person speak highly of New Western.

In high-cost markets like Chicago, that can be tough to meet.If you're looking at a duplex, the self-sufficiency test doesn’t apply, so you’d just need to qualify based on your personal income and the rental income your lender allows.If your current lender isn’t familiar with making FHA work in your situation, it might be worth getting a second opinion from someone experienced with FHA multi-unit financing.

Some of the heavy hitters here in Chicago discussed the ADU program with a very nice person from the building department.

Any insights or personal experiences would be greatly appreciated!

I wouldn’t personally recommend it, as office vacancy rates are currently quite high.

With a loan, a person takes on a Debt Obligation. 

Either way, $600 in cash flow should actually help your personal DTI if you go for conventional financing on a primary again.